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Sorry for the delay in the reply. I tried a breakpoint like you said, but the hang is before the help command gets executed. I poked around in the debugger, and the problem seems to be that the DBRE addon is hanging during startup. I dug into the stack, and found the FelixDispatchQueue thread is hanging trying to open a connection to db.apache.org. This can be traced all the way down to the DBRE addon trying to retrieve the DTD for the .roo-dbre file, http://db.apache.org/torque/dtd/database_3_3.dtd. I'm behind a corporate firewall, so this just hangs.

Apparently some magic happens in the Eclipse environment that makes this work, but I don't know how to get around this for debugging behind our firewall.

EDIT: setting http.proxyHost and http.proxyPort in roo-dev.bat seems to have gotten around the problem.

Attach with a debugger, set a breakpoint to 'help' command entry point and check whether the hang will happen after you reach this entry point or somewhere after it.
The entry point for 'help' command is in project 'org.springframework.roo.shell.osgi', class 'SimpleParserComponent', method 'obtainHelp'.

If you reach the breakpoint in obtainHelp() method, then you can try to debug to to find where the hang happens by stepping-in the code.